Condensation of an aromatic compound with an unsaturated organic compound in the presence of an alkali metal and a peroxy compound



United States Patent CONDENSATION OF AN AROMATIC COMPOUND WITH ANUNSATURATED ORGANIC COM- POUND IN THE PRESENCE OF AN ALKALI METAL AND APEROXY COMPOUND Herman Pines and Vladimir N. Ipatieif, Chicago, 11].,as-

signors to Universal Oil Products Company, Chicago, Ill., a corporationof Delaware No Drawing. Application April 4, 1951, Serial No. 219,315

9 Claims. (Cl. 260-668) This invention relates to the condensation ofunsaturated organic compounds with aromatic compounds and to productsformed thereby. This invention relates more particularly to the sidechain alkylation with an olefin of an alkylaromatic hydrocarbon in whicha carbon atom combined with the aromatic nucleus is also combined withat least one hydrogen atom. The process relates still more specificallyto the side chain alkylation with ethylene of an alkylbenzenehydrocarbon having at least one hydrogen atom combined with a carbonatom in alpha position to the benzene ring.

The condensation of aromatic compounds with unsaturated organiccompounds such as the alkylation of aromatic hydrocarbons with olefinichydrocarbons, has been the subject of many investigations over a longperiod of time. Many different catalysts have been used includingvarious mineral acids and acid-acting compounds but in all of thesereactions, nuclear condensation has always been efiected. Thus in theacid catalyzed alkylation of aromatic compounds having attached to acarbon atom of the ring a saturated carbon atom to which is attached atleast one hydrogen atom, the entering alkyl group attaches to thearomatic nucleus. No direct catalytic method of introducing the alkylgroup into the side chain has been known. Heretofore we accomplishedside chain alkylation of toluene and related alkylaromatic compounds bynon-catalyzed thermal means set forth in our copending applicationSerial Number 152,991 filed March 30, 1950, now abandoned, but thisthermal alkylation process requires high temperatures and high pressuresfor its successful operation.

We have now found that side chain alkylation of toluene and othercarbocyclic aromatic and heterocyclic aromatic ring compounds having anon-olefinic double bond such as pyridine, quinoline, pyrrols, etc. andhaving attached to a nuclear carbon atom a saturated carbon atom towhich is attached at least one hydrogen atom may also be used asstarting materials to elfect side chain alkylation withv an olefin atrelatively lower temperatures and pressures in the presence of acatalyst comprising essentially an alkali metal and an organic peroxycompound. The carbon atom which is attached to the aromatic nucleus ofsaid aromatic compounds is referred to as a saturated carbon atombecause it is a part of a non-olefinic group such as an alkyl group, acycloalkyl group, a cycloalkalkyl group or, an aralkyl group containingno ethylenic bonds or similar unsaturation.

An object of this invention is to react an unsaturated organic compoundwith an aromatic compound selected from the group consisting ofcarbocyclic and heterocyclic aromatic ring compounds having attached toa nuclear carbon atom a non-olefinic or saturated carbon atom to whichis attached at least one hydrogen atom.

An additional object of this invention is to react a monoolefin with analkylaromatic hydrocarbon to form an aromatic hydrocarbon with a longeralkyl group.

ing attached to a nuclear carbon atom a carbon atom of said alkyl groupto which is attached at least one hydrogen atom.

Still another object of this invention is to condense ethylene with thealkyl side chain of an alkylbenzene hy-' drocarbon, said side chaincontaining an alpha carbon atom to which is attached a replaceablehydrogen atom.-

A further object of this invention is to condense ethylene with thecycloalkyl group of a cycloalkylbenzene hydrocarbon, said cycloalkylgroup having a hydrogen atom combined with the carbon atom of thecycloalkyl group which is attached to the aromatic ring.

A still further object of this invention is to provide a process for theside chain alkylation of an alkylaromatic hydrocarbon.

A further object of this invention is to condense ethylene with apolycyclic hydrocarbon having at least one of the rings saturated andhaving at least one hydrogen atom combined with the carbon atom of thesaturated ring which is attached to the aromatic ring.

An additional object of this invention is to provide a method forproducing an aromatic compound containing a long hydrocarbon side chain,said compound being useful in the production of detergents, Wettingagents and the like.

One embodiment of this invention relates to a process which comprisesreacting an olefinic hydrocarbon and an aromatic compound selected fromthe group consisting of carbocyclic aromatic and heterocyclic aromaticring compounds having attached to a nuclear carbon atom a carbon atom ofa hydrocarbon group selected from the group consisting of an alkylgroup, a cycloalkyl group, a cycloalkalkyl group, and an aralkyl groupand to which last named carbon atom is attached at least one hydrogenatom, the process being carried out at condensation conditions in thepresence of an alkali metal and an organic peroxy compound, andrecovering the resultant condensation product.

A second embodiment of this invention relates to a process whichcomprises reacting a non-conjugated olefinic hydrocarbon and an aromaticcompound selected from the group consisting of carbocyclic aromatic andheterocyclic aromatic ring compounds having attached to a nuclear carbonatom a carbon atom of a saturated hydrocarbon group and to which lastnamed carbon atom is attached at least one hydrogen atom at condensationconditions in the presence of an alkali metal and an organic peroxycompound, and recovering the resultant condensation product.

'Another embodiment of this invention relates to a process whichcomprises reacting a monoolefin and an aromatic compound having attachedto a nuclear carbon atom a carbon atom of a saturated hydrocarbon groupand to which last named carbon atom is attached at least one hydrogenatom at condensation conditions in the presence of an alkali metal andan organic peroxy compound, and recovering the resultant condensationproduct.

Still another embodiment of this invention relates to a process forproducing longer chain aromatic hydrocarbons which comprises reacting analkene and an aromatic hydrocarbon having attached to a nuclear carbonatom a carbon atom of a saturated hydrocarbon group and to which lastnamed carbon atom is attached at least one hydrogen atom at acondensation temperature in the presence of a catalyst comprisingessentially sodium and sultant condensation product.

A further embodiment of this invention relates to a process forproducing a longer chain benzene hydrocarbon which comprises reacting analkene and a benzene hydrocarbon having attached to a nuclear carbonatom a carbon atom of a saturated hydrocarbon group and to which lastnamed carbon atom is attached at least one hydrogen atom at acondensation temperature in the presence of a catalyst comprisingessentially sodium and an organic peroxy compound, and recovering theresultant condensation product.

A still further embodiment of this invention relates to a process forproducing a longer chain benzene hydrocarbon which comprises reactingethylene and a benzene hydrocarbon having attached to a nuclear carbonatom a carbon atom of a saturated hydrocarbon group and to which lastnamed carbon atom is attached at least one hydrogen atom at acondensation temperature in the presence of a catalyst comprisingessentially an all-tall metal and an organic peroxy compound, andrecovering a longer chain benzene hydrocarbon from the resultantreaction product.

An additional embodiment of this invention relates to a process forproducing a longer chain benzene hydrocarbon which comprises reactingethylene and a benzene hydrocarbon having attached to a nuclear carbonatom a carbon atom of a saturated hydrocarbon group and to which lastnamed carbon atom is attached at least one hydrogen atom at acondensation temperature in the presence of a catalyst comprisingessentially sodium and an organic peroxy compound, and recovering alonger chain benzene hydrocarbon from the resultant reaction products.

A still additional embodiment of this invention relates to a processwhich comprises catalytically reacting a nonconjugated olefinichydrocarbon and an aromatic compound having a structure represented bythe formula:

wherein Ar represents an aromatic radical having a nucleus selected fromcarbocyclic and heterocyclic nuclei and R and R each separately andindependently represents a member of the group consisting of a hydrogenatom, an allayl group, a cycloalltyl group, and an aryl group and R andR together represent a cycloalltyl group, the process being carried outat a condensation temperature in the presence of a catalyst comprisingessentially an alkali metal and an organic peroxy com pound, andrecovering the resultant condensation product.

Still another embodiment of this invention relates to a process forproducing normal propylbenzene which comprises reacting ethylene andtoluene at a condensation temperature in the presence of a catalystcomprising essentially sodium and an organic peroxy compound andrecovering normal propylbenzene from the resultant reaction product.

Another embodiment of this invention relates to a process for producingnormal propylbenzene which comprises reacting ethylene and toluene at acondensation temperature in the presence of a catalyst comprisingessentially sodium and ditertiary butyl peroxide, and recovering normalpropylbenzene from the resultant reaction product.

An additional embodiment of this invention relates to a process forproducing normal propylbenzene which comprises reacting ethylene andtoluene at a condensation temperature in the presence of a catalystcomprising essentially sodium and cumene hydroperoxide, and recoveringnormal propylbenzene from the resultant reaction product.

The compounds with which unsaturated organic cor-.- pounds are condensedin our process comprise aromatic compounds having attached to a nuclearcarbon atom a carbon atom of a saturated hydrocarbon group to which lastnamed carbon atom is attached at least one hydrogen atom. By the termaromatic compound we mean to include not only alkylated benzenes,substituted benzenes, naphthalenes, and derivatives thereof, but alsoall compounds containing a stable ring or nucleus such as is present inbenzene and which possesses unsaturation in the sense that benzene does,but which has no ethylcnic unsaturation. (Ionsequently it can be seenthat the term aromatic compound, in the sense in which it is used in thespecification and the appended claims, includes not only carbocycliccompounds but also heterocyclic compounds having stable nuclei. Thecarbocyclie compounds may have a benzene, naphthalene, etc. nucleus. Theheterocyclic aromatic compounds may have a pyridine, furan, thiophene,pyrrole, pyrazole, etc., nucleus. In addition, the aromatic compoundcontemplated for use in our process may contain both a carbocyclic ringand a heterocyclic ring such as is found in indole and in carbazole.Also, the aromatic compounds may contain both a benzene nucleus and acycloalltane nucleus such as is found in tetralin and in indan.

As hereinbefore stated, the aromatic compounds preferred for use in ourprocess contain a saturated side chain, said chain being attached to anuclear carbon atom by a saturated carbon atom, i. e., a carbon atomthat is bonded by univalent bonds to four atoms. The saturated carbonatom should have at least one hydrogen atom attached thereto. Theserequisites arc desirable for the reason that aromatic compounds, such ast butylbenzene, which do not have a hydrogen atom attached to the alphacarbon atom, show very little tendency under the conditions of operationemployed in our process to undergo condensation of the type hereintaught. Similarly, styrene, in which the alpha carbon atom in the sidechain is unsaturated, does not condense with unsaturated organiccompounds in the manner herein specified. Thus the preferred aromaticcompounds are those in which the alpha carbon atom of the side chain issaturated and in which said alpha carbon atom has at least one hydrogenatom attached thereto. The side chain may comprise only one carbon atom,as the methyl group in toluene, or it may comprise a number of saturatedcarbon atoms in straight chain or branched chain relation such as thenormal butyl radical or the isobutyl radical in normal butylbenzene andisobutylbenzene, respectively. The substituent need not necessarily bean aliphatic chain; it may be a cycloalkane radical as in tetralin or asin cyclohexylbenzene or an aralkyl group as a benzyl group as indiphenylmethane.

Suitable alkylaromatic hydrocarbons include toluene, ethylbenzene,normal propylbenzene, cumene, normal and secondary butylbenzene,methylnaphthalene, and the like. Other suitable aromatic hydrocarbonsinclude tetralin, indan, diphenylmethane, cyclopentylbenzene, and

methylethylbenzene.

The aromatic ring in the compounds herein referred to may contain othersubstituents such as a chloro group, a methoxy group, an ethoxy group, anitro group, and the like.

The aromatic reactants employed in our process are condensed withnon-conjugated unsaturated organic compounds. The unsaturated organiccompounds are olefinic in character and include monoolefins andparticularly ethylene. For the purposes of this invention, aromaticcompounds such as benzene are not regarded as being unsaturated.Examples of unsaturated organic compounds suitable for use in thisprocess include monoolefins such as ethylene, propylene, l-butene,Z-butene, and isobutylene, monoolefins of higher molecular weight:non-conjugated dienes such as 2,5-dimethyl-1,6-hexadiene andnon-conjugated polyolefins containing more than two pairs of doublebonds per molecule; unsaturated ketones such as mesityl oxide, andcompounds such as allyl amine, allyl cyanide, acrylonitrile, alphacyanoacrylonitrile, and the like.

Catalysts which are useful in this process include a combination of analkali metal or ofseveral alkalimetals and at least one organic peroxycompound. Of the alkali metals: lithium, sodium, potassium, rubidium andcesium; the more plentiful sodium and potassium are generally preferredand particularly sodium because of its relatively lower cost. Thesealkali metals are utilized together with an organic peroxy compound, Thepresence of both an alkali metal and one or more of the mentioned classof organic peroxy compounds which decompose to form free radicals isnecessary for effecting the combination or condensation of an olefinsuch as ethylene with the alkyl side chain or other saturated side chainof a carbocyclic or heterocyclic aromatic ring compound having attachedto a nuclear carbon atom a saturated carbon atom to which is attached atleast one hydrogen atom.

The organic peroxy compounds which are useful as catalyst components inthis process include acetyl peroxide, benzoyl peroxide,ascaridole,.ditertiarybutyl peroxide and also various hydrocarbonhydroperoxides such as tertiarybutyl hydroperoxide, tetralinhydroperoxide, methylcyclopentyl hydroperoxide, dimethylcyclopentylhydroperoxide and various other hydroperoxides and peroxides which areformed by oxidation of olefinic and parafiinic hydrocarbons as well ascertain aromatic and naphthenic hydrocarbons. Azo compounds, such asambenzene, and diazo compounds are also usable in this process.

Better contacting of the reactants and catalysts and improved yields ofdesired products are sometimes effected by mixing peroxy compound with acatalyst supporting or spacing material such as activated charcoal; alsogranular coke, silica, alumina, pumice, porcelain, quartz, etc.; steelturnings, copper shot, etc. which do not have an adverse influence onthe reaction but improve the mixing. Such spacing materials are usefulin either batch type operation as in an autoclave or in continuoustreatment in a tubular reactor or other suitable apparatus.

The process of this invention is carried out using either batch orcontinuous types of operation in suitable equipment such as autoclavesor tubular reactors constructed from steel or glass lined steelreactors. The process is carried out at a temperature of from about 100to about 350 C. and preferably at a temperature of from about 150 toabout 275 C. at a pressure of from about 5 to about 50 atmospheres. Whenthe stirring or mixing of the reactants and catalyst is very thoroughand efficient, the process may be carried out readily at a temperatureof 125 C. and at a pressure of 5 atmospheres, but higher temperaturesand pressures are preferred when the mixing is less eflicient. Theoperating temperature and pressure will also be dependent upon thearomatic and olefinic hydrocarbons charged and upon the ratios ofreactants present in the reaction zone, as Well as upon the catalystpresent.

In order to promote the primary side chain alkylation, that is, toattach only one alkyl group to the alkyl side chain and in someinstances to decrease the loss of olefin through undesired sidereactions, it is generally preferred to employ an excess of aromatichydrocarbon to olefin such as ethylene in this process. In other words,the preferred ratio of aromatic hydrocarbon to olefinic hydrocarbon isgreater than one.

The amount of catalyst used in the process is dependent upon the natureand reactivity of the aromatic hydrocarbon undergoing side chainalkylation and upon the nature of the olefin used as alkylating agent.Also the particular catalyst promoter has an influence upon the amountof alkali metal necessary for efficient operation of the process. Ingeneral from about 0.05 to about 0.5 atomic proportion of alkali metalis present per molecular proportion of alkylaromatic hydrocarbon orother side chain alkylatable hydrocarbon present in the reaction zone.Also from about 0.1 to about 5 mole per cent of an organic peroxycompound is employed per molecular proportion of alkylaromatichydrocarbon present in the reaction zone. The amounts of alkali metaland peroxy compound used are not critical and depend upon other factorssuch as the hydrocarbons to be alkylated, the operating conditions,e'tc.-

In carrying out the process the olefinic hydrocarbon charged such asethylene may be introduced continuously or intermittently, the lattermethod being commonly employed in the usual type of batch operationconducted in an autoclave so that the consumption of ethylene can hefollowed by observing the decrease in operating pressure of theautoclave as the reaction progresses. After the reaction has reached thedesired stage of completion, the reaction products are discharged fromthe autoclave, unconverted olefin such as ethylene is recovered forfurther use in the process or utilized for some other purpose.

The mixture of reaction products is then subjected to suitableseparation treatment such as filtration to remove unconsumed alkalimetal catalyst followed by fractional distillation of normally liquidproducts to separate unconverted charging stock from side chainalkylated prodnets and higher boiling materials, the latter beingsometimes formed as by-products of the reaction.

In this process one molecular proportion of olefin such as ethylene andone molecular proportion of alkylaromatic hydrocarbon as toluene reactin the presence of a catalyst as referred to herein to form a longerchain alkylaromatic hydrocarbon as illustrated by the followingequation:

t CH; H-CCH2CH3 Catalyst C H2 C HQ Toluene E thylenc n-Propylbenzene Theresultant reaction product such as n-propylbenzene may sometimes reactwith a further molecular proportion of olefin as ethylene to form astill longer chain alkylaromatic hydrocarbon as indicated in thefollowing equation:

Catalyst n-propylbenzene Ethylene 3-phenylpentane Other alkylaromatichydrocarbons and cycloalkylaromatic hydrocarbons may be reactedsimilarly with ethylone to produce longer chain alkylaromatichydrocarbons from one molecular proportion of the charged alkylaromatichydrcarbon and one, two or more molecular proportions of the olefin.

The longer chain alkylaromatic hydrocarbons and other products formed bythe process of this invention are useful as intermediates in theproduction of detergents, resins, insecticides, etc. For example atridecyl benzene which is formed by condensing toluene with dodecene(propylene tetramer) or by condensing n-butylbenzene or sec- 1butylbenzene with propylene trimers may be sulfonated by strong sulfuricacid and then neutralized with a base to form a detergent. Othercondensation products of this process may be chlorinated to formeffective insecticides,

fungicides, etc.

The nature of this invention is illustrated further by the followingexamples which should not be misconstrued to limit unduly the generallybroad scope of the invention.

Example I A glass lined rotatable .steel autoclave of 850 cc, ca;

pacity was charged with 92 grams (1 mole) of toluene, 6.7 grams (0.3-mole) of sodium and 2 grams of ditertiarybutyl peroxide (0.01 mole)after which the autoclave Was closed and ethylene was then introducedthrough a control valve to an initial pressure of 30 atmospheres. Theautoclave and its contents were then heated at a temperature of 200 to250 C. for a time of 4 hours. After the autoclave and reaction mixturehad cooled to room temperature, the product was removed from theautoclave, filtered to remove sodium, and the filtrate was fractionallydistilled. The fractional distillation treatment separated the reactionproduct into 58 grams (0.63 mole) of unconverted toluene, 28 grams (0.26mole) of normal propylbenzene and 4 grams (0.03 mole) of3-phenylpentane. The yield of normal propylbenzene was 76 mole percentbased upon the amount of toluene which reacted.

Example II The autoclave employed in Example I was charged similarlywith 92 grams (1 mole) of toluene, 6 grams (0.26 mole) of sodium and 10grams (0.09 mole) ofdi-isobutylone containing some peroxides whichformed therein by oxidation during storage. The autoclave was thenclosed and ethylene was admitted through a control valve to a pressureof 30 atmospheres. The charged autoclave was then heated to 200 to 250C. for 5 hours after which it was permitted to cool to room temperature.

The reaction product obtained was separated into 73 grams (0.8 mole) ofrecovered toluene, 5.5 grams (0.05 mole) of n-propylbenzene, and 2.5grams of higher boiling product.

Example 111 The autoclave employed in Examples I and II was charged with92 grams of toluene, 7.8 grams of sodium, 3.2 grams of cumenehydroperoxide (0.02 mole) and suificient ethylene to give a pressure of30 atmospheres at a temperature of C. The charged autoclave was thenheated at a temperature of 200229 C. for a time of 5.75 hours afterwhich the autoclave was cooled to room temperature. The unconvertedethylene was released from the autoclave and the resultant reactionproduct was removed from the autoclave and investigated. It was foundthat 10% of the toluene had reacted to give 6.5 grams of normalpropylbenzene, a yield of 54% based upon the toluene which reacted. Also3.7 grams of higher boiling product was obtained.

Example IV The autoclave employed in the preceding examples was chargedwith 92 grams of toluene, 6.7 grams of sodium, 2 grams of azobenzene(0.01 mole) and ethylene to give a pressure of atmospheres at 20 C. Thecharged autoclave was then rotated and heated at a temperature of200-229 C. for a time of 3.5 hours after which the autoclave was cooledto room temperature. Residual gases amounting to 19.1 liters andcontaining 0.4 liter of ethane were released from the autoclave. Theliquid reaction products were taken from the autoclave and found tocontain 5.4 grams of normal propylbenzene and 2.5 grams of higherboiling product. As 9.8 grams of the charged toluene had reacted, thenormal propylbenzene produced represented at 46 mole percent yield.

We claim as our invention:

1. A process which comprises reacting a non-conjugated olefinichydrocarbon and an aromatic compound selected from the group consistingof carbocyclic aromatic and heterocyclic aromatic ring compounds havingattached to a nuclear carbon atom a carbon atom of a saturatedhydrocarbon group and to which last named carbon atom is attached atleast one hydrogen atom at a temperature of from about 100 to about 350C. and a pressure of from about 5 to about 50 atmospheres in thepresence of an alkali metal and of an organic peroxy compound, andrecovering the resultant condensation product.

2. A process which comprises reacting a non-conjugated olefin and anaromatic compound having attached to a nuclear carbon atom a carbon atomof a saturated hydrocarbon group and to which last named carbon atom isattached at least one hydrogen atom at a temperature of from about toabout 350 C. and a pressure of from about 5 to about 50 atmospheres inthe presence of an alkali metal and of an organic peroxy compound, andrecovering the resultant condensation product.

3. A process which comprises reacting a non-conjugated olefinichydrocarbon and an aromatic compound selected from the group consistingof carbocyclic aromatic and heterocyclic aromatic ring compounds havingattached to a nuclear carbon atom a carbon atom of a hydrocarbon groupselected from the group consisting of an alkyl group, a cycloalkylgroup, a cycloalkalkyl group, and an aralkyl group and to which lastnamed carbon atom is attached at least one hydrogen atom, the processbeing carried out at a temperature of from about 100 to about 350 C. anda pressure of from about 5 to about 50 atmospheres in the presence of analkali metal and an organic peroxy compound, and recovering theresultant condensation product. i

4. A process for producing longer chain aromatic hydrocarbons whichcomprises reacting an alkene and an aromatic hydrocarbon having attachedto a nuclear carbon atom a carbon atom of a saturated hydrocarbon groupand to which last named carbon atom is attached at least one hydrogenatom at a temperature of from about 100 to about 350 C. and a pressureof from about 5 to about 50 atmospheres in the presence of sodium and anorganic peroxy compound, and recovering the resultant condensationproduct.

5. A process for producing a longer chain benzene hydrocarbon whichcomprises reacting ethylene and a benzene hydrocarbon having attached toa nuclear carbon atom a carbon atom of a saturated hydrocarbon group andto which last named carbon atom is attached at least one hydrogen atomat a temperature of from about 100 to about 350 C. and a pressure offrom about 5 to about 50 atmospheres in the presence of an alkali metaland an organic peroxy compound, and recovering a longer chain benzenehydrocarbon from the resultant reaction product.

6. A process for producing a longer chain benzene hydrocarbon whichcomprises reacting ethylene and a benzene hydrocarbon having attached toa nuclear carbon atom a carbon atom of a saturated hydrocarbon group andto which last named carbon atom is attached at least one hydrogen atomat a temperature of from about 100 to about 350 C. and a pressure offrom about 5 to about 50 atmospheres in the presence of sodium and anorganic peroxy compound, and recovering a longer chain benzenehydrocarbon from the resultant reaction product.

7. A process for producing a longer chain benzene hydrocarbon whichcomprises reacting ethylene and toluene at a temperature of from about100 to about 350 C. and a pressure of from about 5 to about 50atmospheres in the presence of an alkali metal and an organic peroxycompound, and recovering a longer chain benzene hydrocarbon from theresultant reaction product.

8. A process for producing normal propylbenzene which comprises reactingethylene and toluene at a temperature of from about 100 to about 350 C.and a pressure of from about 5 to about 50 atmospheres in the presenceof sodium and ditertiary butyl peroxide, and recovering normalpropylbenzene from the resultant reaction product.

9. A process for producing normal propylbenzene which comprises reactingethylene and toluene at a temperature of from about 100 to about 350 C.and a 9 pressure of from about 5 to about 50 atmospheres in the presenceof sodium and cumene hydroperoxide and recovering normal propylbenzenefrom the resultant reaction product.

References Cited in the file of this patent UNITED STATES PATENTS 10Hanford et al. June 18, 1946 Whitman Sept. 7, 1948 Little Apr. 10, 1951Ladd et a1. May 15, 1951 Erchak Nov. 24, 1953

1. A PROCESS WHICH COMPRISES REACTING A NON-CONJUGATED OLEFINICHYDROCARBON AND AN AROMATIC COMPOUND SELECTED FROM THE GROUP CONSISTINGOF CARBOCYCLIC AROMATIC AND HETEROCYCLIC AROMATIC RING COMPOUNDS HAVINGATTACHED TO A NUCLEAR CARBON ATOM A CARBON ATOM OF A SATURATEDHYDROCARBON GROUP AND TO WHICH LAST NAMED CARBON ATOM IS ATTACHED ATLEAST ONE HYDROGEN ATOM AT A TEMPERATURE OF FROM ABOUT 100* TO ABOUT350* C. AND A PRESSURE OF FROM ABOUT 5 TO ABOUT 50 ATMOSPHERES IN THEPRESENCE OF AN ALKALI METAL AND OF AN ORGANIC PEROXY COMPOUND, ANDRECOVERING THE RESULTANT CONDENSATION PRODUCT.